I'd definitely go with the dig deeper idea.

Is he being intellectually challenged? Are there issues at the new school? Bullies?

It could be a sign of needing more personal control.

It could be a type of self-destructive behavior, where a low sense of self worth gets reinforced through procratination and the ensuing negative consequences. Depression and self hate are on this path.

It could be a thrill seeking behavior, such that doing something at the last minute is exciting. The more drastic the consequences the more exciting the challenge.